Unexpected switch in regioselectivity of tether-directed Bingel-type biscyclopropanations depending on the leaving groups at tethered active methylene moieties‡

Literature Information

Publication Date 2003-01-08
DOI 10.1039/B211337F
Impact Factor 6.222
Authors

Tetsuo Hino, Kazuhiko Saigo


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Abstract

The regioselectivity of tether-directed Bingel-type biscyclopropanations of [60]fullerene was switched depending on the leaving groups at tethered active methylene moieties; the reactions of [60]fullerene with unhalogenated tethered bis(active methylene) derivatives/I2 and with brominated derivatives in the presence of 1,7-diazabicyclo[5.4.0]undec-7-ene gave trans-4-adducts predominantly, while the reactions with chlorinated derivatives afforded equatorial-adducts almost exclusively.

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